The iTunes Hairball

Among Sun Microsystems (now Oracle something or other) founder Scott NcNealy’s favorite potshots at Microsoft was calling Windows a “hairball.” Know what? iTunes is a bigger hairball.

That a company hasn’t come along and blown the iTunes music jail out of the water is mind blowing.

iTunes is highly restrictive and unintuitive. Maybe I am unintuitive. It’s me or iTunes, but I have loathed it for some time.

Here’s what I want: to login into the cloud and access my music (photos, videos, name it)  no matter what device I am using or where I am.

What I get from iTunes is music that disappears, music  that won’t easily move from device to device and an interface that is hard to use.

Beware, getting a new computer risks rocking your music world and not in a good way.

The most recent saga included acquiring new desktop and an iPhone. Let me start with the desktop, which happened first and around Christmas time. I had already experienced problems with iTunes on my an iPad acquired in the middle of last year. Sometimes, the music store would not download. The menus confused me. I couldn’t easily find stuff.

So moving my 2,600 song-strong music library on iTunes from my old desktop to the new unit scared me. It turned out not to be so bad. I authorized the new desktop as one of my five allowed iTunes repositories and bingo, all my purchased music magically showed up.

That provided a new home base for all my tunes for downloading to iPad, iPod and iPhone. All the music CDs I had transferred from CDs were gone, but I could, over time, download it again.

Just as magically, all that music vanished about a month later. It wasn’t in a folders on my PC. It simply vanished. Poof. Gone.

I was perplexed. Where was it? Was changing my e-mail login responsible for my loss? How did this happen? Who could I call? I have no idea. My purchase records were all there, but the music was gone.

My Apple friends made several suggestions. Just purchase all the music again and I would not be charged because Apple had a record of what I had bought. I tried that on one album and it appeared I was charged.

Download in reverse, another suggested, from the iPod to iTunes. There are plenty programs that allow you to flow music from your iPod (my music was still on that) back into iTunes. I tried a program – that was too difficult and time consuming.

I laid off for while to ponder the problem. Meantime, I bought a Verizon iPhone. It is a truly remarkable device, but I stayed away from downloading music because it would bring into contact with hairball – iTunes.

After a few days, it occurred to me that this could be easy, I thought. I’ll just download from my old PC which had iTunes and all my music. So I set the eight-year Dell machine back up and hooked my iPhone into it. iTunes told me it could not recognize the device until I downloaded an upgraded version. I tried and failed several times to do this.

Then with the old desktop, I tried burning my music to a backup DVD, which I could use to download the music into my new desktop. The DVD initialized and starting burning the first song. Then the process would cancel for an “unknown” reason. Certainly, it was unknown to me with the two brands of DVD I tried.

Then I tried Home Sharing from the old PC to a laptop so I could download the music from the fomer. iTunes does not let you do that – at least me, anyway.

Finally, I was able to upgrade iTunes on my old PC, but the aging unit still would not download the music to my new iPhone. I pored through the menus, checking off everything in sight. Finally, it worked. iTunes started downloading song 1 of 2,600 to my iPhone. In 90 minutes, all my music was on my beloved iPhone.

What a headache, though! Why couldn’t I just have all my music in the cloud and easily access whenever I want it?

Has anyone else choked on the iTunes hairball like I have?

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27 comments On The iTunes Hairball

  • I’ve noticed a number of issues when dealing with new devices on older systems, especially since they updated iTunes to 10x. I’m getting my teachers up on iPads and I’ve had to upgrade them to new systems as well as the first generation of Intel Macs seems to have issues with updating iTunes and recognizing the iPads.

    I’ve managed to backup my library to a firewire drive in the past, which made for very easy porting to a new system.

    You mention the software for a backwards update. Did you try Senuti? It’s free and extremely easy to use.

  • That’s probably a smart move…but unnecessary if your music and such was securely and conveniently in the cloud.

  • I had a recent hard drive failure (I always intended to image my HD) which required a new install of WIN 7 (64b). ITunes worked great before but now I can not get it to work– it will not recognize my IPhone and locks up. ITunes C/Support tried for hours to get it working. Even their second tier C/S could not fix the problem. The only change I made on my desktop was a new HD. Additionally, I, too, find the ITunes interface unintuitive.

  • I find it very difficult to get songs to show up in iTunes. I purchased an album recently on line. It downloaded to a “Download” file on my computer. I tried to import it into iTunes. It wouldn’t let me import the whole folder–just one song at a time. Frustrating. I think iTunes looks antiquated as well.

  • The joy of iTunes. I use an old sony mp3 player for jogging. I hook it up to my computer with a USB cable and I drag and drop my music in folders or playlists or both. I can do that with my laptop, my wifes laptop or my desktop.
    Why can’t it be that easy with my iPod touch????
    But we only have ourselves to blame. We keep buying the Apple products. Until we all make a stand and switch to another product it won’t end.

  • I hate iTunes. I have no idea how to get it with all my music on my new computer not to mention loading another device. But let me ask. If you dislike it that much, why do you have all the i devices??????????

  • So John, where do you store your music on the cloud ?
    I use Amazon VOD for my videos, that I can access anywhere,
    but I’d like to do something like that for my music, what do you
    recommend ?

  • OMG! HAIRBALL!! That’s the new bad word I’m going to yell when this monstrosity snags me again on something I think should be SO SIMPLE and yet…
    I have just learned to live with itunes and it’s personality quirks; like a dimwitted relative: I can’t really just throw ’em out on the street, but I can’t figure ’em out or fix ’em either….

  • I’ll try Senuti, Chris. In the end, my old desktop is my main iTunes machine – forever til it or I die.

  • I have always hated Itunes. Tried it once and it took over my computer, so when I reformatted I got rid of it. Luckily, I did not store my music on it. When I got a little ipod, I searched around the internet and found another program I could use to transfer my music. Don’t have either now, so can’t remember what it was. But I refuse to use Itunes, or even the over rated ipods

  • You must be an idiot. Don’t you back up your stuff? I have 6,150 songs on my computer. Some bought from iTunes, some ripped from CD’s, some aquired via Limewire/Frostwire, some extracted from Youtube videos. I’ve never “lost” anything from switching to a new computer or new OS. If you “lose” all your music because you bought a new machine and left everything on the old one without backups, and couldn’t figure it out for several days, then I seriously doubt you have any business writing a computer related column.

  • Yes, I am an idiot, having written about computers for 30 years (editor of PC Week for 16 years, tech columnist for WSJ and Boston Globe for sevens years). So lose the attitude that so many of you nerds seem to have. I guesstimate I’ve written 4,000 tech columns and hundreds more blog posts if longevity says anything.

    Also, I just have a life and prefer not to spend inordinate amount of time screwing around with this stuff. My 2,500 songs are not my life, but something I wanted to get back and from the comments here, others seem to have had the same problems as me w iTunes. I guess we’re just not as smart you, Marky Mark.

  • Apart from it being a hairball, which it most certainly is, my other big gripe is that you can’t re-download without paying again if you lose stuff. And the backing up is a pain- I wish I could find a way of backing up on my external hard drive instead of discs. I mainly use my ipod for audiobooks, but have gone to Audible dot com instead now. You can download as often as you want from them.

  • A very nice product is Spotify. All your music is in the cloud.

  • Thanks for the suggestion, Ted….

  • So John, where do you store your music on the cloud ?
    I use Amazon VOD for my videos, that I can access anywhere,
    but I’d like to do something like that for my music, what do you
    recommend ?

  • I don’t see the problem here at all. I’ve got itunes running on a win7 PC and a second copy on a winXP laptop. The music was originally downloaded and ripped to the win7 box, where it all landed neatly in the My Music folder for my login. When I decided I wanted the whole lot accessible to both my PCs I copied the whole of the My Music folder to a Samba share on a Ubuntu box, and told the itunes on the win7 box to look for it there. It just works.

    As for backup, I copied the whole of the shared drive on the server to an external HD. Again, it just works. This is for a library of 40000+ songs.

    Only real gripe is the stuff that was bought when itunes store was copy protected won’t play other than on my ipod or itunes, reducing what I can share to my uPnP devices via Twonky, but even this doesn’t apply to new downloads.

  • So John, where do you store your music on the cloud ?
    I use Amazon VOD for my videos, that I can access anywhere,
    but I’d like to do something like that for my music, what do you
    recommend ? I’ve asked this question 3 times now, no response.

  • Just another thing to add (and I agree about the whole unintuitive thing) – Ubuntu…or any other flavour of Linux. No support at all. I have to have an old copy of WIN XP as a 2nd OS just to backup/restore my Ipod.



  • Just another thing to add (and I agree about the whole unintuitive thing) – Ubuntu…or any other flavour of Linux. No support at all. I have to have an old copy of WIN XP as a 2nd OS just to backup/restore my Ipod.



  • Although Marky Mark does have a little attitude, I do have to agree with him in the fact that you have a certain responsibility to yourself when upgrading to a new computer to backup things that are important to you. especially things such as music when you think about it takes alot of your time to compile. I have over 3000 songs and although it is not my life, It would be a real pisser if I lost them.

  • Agreed, Martin but I tried and failed for unknown reasons. Point remains: iTunes = frustration

  • I recently purchased and iPad which I love. Unfortunately, it is tied to iTunes also with all the frustrations that John described. On the other hand, I have an Android phone that is NOT tied to iTunes. I figure in about 6 months, new Android devices and an improved Android tablet app list will allow me to dump the iPad and go Android.

  • Wow…that’s ditching the iPad pretty quick. I have an iPhone and have reviewed many Android phones. The iPhone is so much more polished than the Android phones. It’ll be interesting to see if Android can catch up given it’s openbess versus the tightly-controlled Apple architecture.

  • I like the hairball quote. yes it was a trick when I installed a new hard drive, but had a back up to use … I used music match for years quite successfully & could transcribe tapes and disc’s with it too… with i tunes to make an MP3 it translates to MP3 but the annoying thing is it then places a dup in the library..yet hard to tell which is the MP3 copy. somehow I have managed to get three and four mp3 copies itunes never telling me I already have one…. I actually miss music match that yahoo bought and eliminated…. it worked quite well… hairball yes that is it.

  • Yes, the iPhone is absolutely great, and yes, iTunes absolutely sucks. The iPhone is why I have both. The iPhone just has the best music/video playback I have seen. If I watch or listen on my computer, I use a different player.

    I have over 160,000 songs, which has over 16,000 different albums. Do not rely on iTunes. Buy or acquire your music, save it in your music folder, and back it up. Save all your music there, then add that folder to the iTunes library. If you add music, save the file to your music folder and add that folder. If you buy from iTunes, good luck finding where iTunes will hide your file. Once you find it, move it to somewhere you can find it, like your music folder, then add that folder.

    I realized the problem after buying games and trying to move them with a new computer build. I couldn’t find them. They were there, the automatic transfer built into windows 7, moved them to the right spot, thank god. I still haven’t found where they were moved to. Also, if you buy it through iTunes, you may have trouble moving it to another apple device because you buy it for that device, not just buy it outright(I Believe).

  • You have another ‘thumbs down’ here as well. I, also, am stuck to that piece of garbage {and it is a piece of garbage) iTunes because of my iPad. As a result of it’s behavior, I find myself reluctant to use it when I have to add something to my iPad…like a kid with cod liver oil.

    PS…I make no ‘purchases’ , however, when checking my PayPal account recently, I found a few unauthorized payments of 9.98…so…not only don’t I like iTunes in general, it now gives me a reason to find it despicable!!!

    If anyone knows of something else I can use for iPad, please let me know!!! Thanks.

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